Carbon acidity and ring strain: A hybrid HF-DFT approach (becke3LYP/6- 311++G**)

Tetrahedron

Volumn 53, Issue 28, 1997, Pages 9741-9748

  Alkorta, Ibon ^a   Elguero, José ^a  

^a INSTITUTO DE QUÍMICA MÉDICA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

DIAZONIUM COMPOUND; TETRAHYDROFURAN;

ARTICLE; CATALYSIS; ION EXCHANGE; POLYMERIZATION; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

EID: 0030850015     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00597-8     Document Type: Article

References (24)

1. March, J. Advanced Organic Chemistry, Fourth Edition, Wiley, New York, 1992, pp. 250-252, 319, 756.
2. Cram, D. J. Fundamentals of Carbanion Chemistry, Academic Press, 1965, pp. 48-50.
3. Gau, G.; Assadourian, L.; Veracini, S. Prog. Phys. Org. Chem. 1987, 16, 237.
4. Buncel, E.; Durst, T. Comprehensive Carbanion Chemistry, Elsevier, New York, 1980.
5. Knipe, A. C. Org. React. Mech. 1988, 357.
6. Alkorta, I.; Elguero, J.; Rozas, I.; Balaban, A. T. J. Mol. Struct. (Theochem) 1990, 208, 63.
7. Alkorta, I.; Elguero, J.; Rozas, I.; Balaban, A. T. J. Mol. Struct. (Theochem) 1990, 206, 67.
8. Notario, R.; Elguero, J. J. Chem. Soc. Chem. Commun. 1995, 1543.
9. NIST Standard Reference Database 19B and NIST Negative Ion Energetic Database, Version 2.06. Original data from Lias, S. G.; Bartmess, J. E.; Liebman, J. F.; Holmes, J. L.; Levin, R. D.; Mallard, W. G.; J. Phys. Chem. Ref. Data 1988, 17, Suppl. 1.
10. Hare, M.; Emrick, T.; Eaton, P. E.; Kass, S. R. J. Am. Chem. Soc. 1997, 119, 237.
11. Dixon, R. E.; Streitwiser, A.; Williams, P. G.; Eaton, P. E. J. Am. Chem. Soc. 1991, 113, 357.
12. Minkin, V. I.; Glukhovtsev, M. N.; Simkin, B. Ya. Aromaticity and Antiaromaticity, Wiley, New York, 1994 and references therein.
13. Cremer, D.; Kraha, E.; Szabo, K. J. in The Chemistry of the Cyclopropyl Group, Rappoport, Z., Ed., Wiley, New York, 1995, Vol. 2.
14. Alcamí, M.; Mó, O.; Yáñez, M. Molecular Electrostatic Potentials: Concepts and Applications. Theoretical and Computational Chemistry, Murray, J. S.; Sen, K. Eds., Elsevier Science B.V., 1996, Vol. 3.
15. Burk, P.; Abboud, J.-L. M.; Koppel, I. A. J. Phys. Chem. 1996, 100, 6992.
16. Klicik, J.; Rubin, Y.; Breslow, R. Tetrahedron 1997, 53, 4129 and references therein.
17. Balaban, A. T.; Banciu, M.; Ciorba, V. Annulenes, Benzo-, Hetero-, Homo-Derivatives and their Valence Isomers, CRC Press, Boca Raton, 1987, Vol. 2.
18. Abboud, J.-L. M.; Herreros, M.; Notario, R.; Mó, O.; Yáñez, M.; Regitz, M.; Elguero, J. J. Org. Chem. 1996, 67, 7813.
19. Bader, R. F. W. Atoms in Molecules. A Quantum Theory, Oxford University, New York, 1990.
20. Mole, S. J.; Zhou, X.; Liu, R. J. Phys. Chem. 1996, 100, 14665.
21. Korth, H.-G.; Sicking, W. J. Chem. Soc. Perkin Trans. 2 1997, 715.
22. Gaussian-94 , Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian, Inc.: Pittsburgh, PA, 1995.
23. Krishnam, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1984, 80, 3265
24. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.